


Double Trouble

by Taybay14



Category: Supernatural
Genre: A/B/O, Alpha Dean Winchester, Alpha/Beta/Omega Dynamics, Cas and Jimmy are pretty much shameless sluts, Claiming, Claiming Bites, Daddy Kink, Knotting, M/M, Omega Castiel (Supernatural), Omega Castiel/Alpha Dean Winchester, Omega Jimmy Novak (Supernatural), Possessive Dean, Rough Sex, Size Difference, Size Kink, Slut Shaming, Smut, Threesome, Tiny Omegas, Tumblr Prompt, Twincest, Twink Castiel (Supernatural), Twink Jimmy Novak, belly bulge, face fucking, porn with the tiniest bit of plot, slick
Language: English
Status: Completed
Published: 2019-11-03
Updated: 2019-11-03
Packaged: 2021-01-21 08:53:57
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,706
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21296816
Author URL: https://archiveofourown.org/users/Taybay14/pseuds/Taybay14
Summary: A nice, smutty prompt fill for my anon that's been asking for tiny omegas Cas/Jimmy seducing their college professor/alpha Dean, with lots of size kink/belly bulging. Pretty much just shameless smut. Enjoy (;
Relationships: Castiel/Dean Winchester, Castiel/Jimmy Novak, Castiel/Jimmy Novak/Dean Winchester, Jimmy Novak/Dean Winchester
Comments: 28
Kudos: 468





	Double Trouble

Dean is running late. Seriously late. He’s pretty sure he left the textbook for this class back in his office, he already spilled his coffee, and even though it’s the first day of fall semester, he’s already had to fend off Michael twice now, a beta and fellow professor in his department that hates taking no for an answer. 

Suffice to say, he’s flustered as he shows up to his engineering 101 class four minutes late. The talking dies down as he hurries over to the desk in the front and practically dumps all of his stuff on it. Taking a deep breath, he places his hands on the desk and smiles up at the class. “So, anyone else hate Mondays?”

The students all laugh, and he watches as they relax in their seats, already figuring out that Dean’s one of the cool professors. Dean grabs his stack of syllabi and starts handing them out to the person at the start of each row. He’s about halfway up the stairs when he hands one to a small hand that purposely brushes against his fingers. Dean flicks his eyes up and has to pause for a moment until he remembers how to breathe. 

Two gorgeous little things are sitting there, one leaning forward so he can look over the other’s shoulder at Dean. They’re identical twins. Which just… just isn’t fair. He can barely handle one dose of their messy bed-head that reminds him of lazy Sunday mornings, where he’d have them naked… or maybe in a silk nightie, all stretched out and sleepy as he fucks them. He can barely handle one dose of those soft pink lips that puff out just slightly more than they should as he imagines how good they’d look wrapped around his cock. 

Add in the delicate features, long eye lashes, subtly flushed cheeks, and those big, blue disney-princess eyes, and Dean’s a goner. 

Add in the fact that they’re both So. Damn. Small. - like to the point he’d have to remember to double check their IDs before fucking them - and Dean’s rock hard in his pants. 

Add in that the two of them smell like needy little omegas that are clearly aroused, and he’s ready to call the class for the day and take them up to his office to fuck and knot and claim. 

“Thank you,” the one closest to him says in a lullaby voice that makes Dean’s breath hitch. 

“Y - you’re - you are welcome. Okay.” He stares at them for a few more seconds before forcing himself to take a step back. “Okay. Yeah. Okay.”

He has no idea, but when he finally manages to turn around and continue, the twins exchange a look that is a silent agreement. That alpha is theirs. Poor guy just doesn’t know it yet. 

\---- 

Dean lasts two more classes, which, if you ask anyone around, is fucking impressive. Those boys are out to kill him. Between their slutty outfits, bedroom eyes, and pencils they keep sucking on, Dean’s not sure how he made it this long. 

Today, he’s giving up. They walk into his lecture hall, both wearing these little lace shorts that show off the curves of their butt cheeks, as well as cut-off tanks that show off their pale bellies. Dean can practically see his cock inside them. Can see those bellies bloated with his cum, poking out from beneath the fabric of their shirts. 

He already checked their school IDs online - they’re both 18. He doesn’t know why they’re so fucking tiny, tinier than normal omegas, but he doesn’t care. Dean just needs to fuck them. Now. 

Making a promise to himself that he’ll only fuck each of them once, just to get them out of his system, Dean ends class a few minutes early. 

“Mr. and Mr. Novak, can I speak with you two for a moment?” Dean asks in a surprisingly clear, calm voice. 

The two boys share a knowing smile before sashaying down the stairs and over to his desk. One of them walks around his desk and hops up so he’s sitting on the edge, looking up at Dean with pupils blown from lust. The other sidles up next to Dean, pressing his body against the alpha without caring that it’s inappropriate. Both nibble on their plump, pink bottom lip as they wait to see what their professor wants with them. 

“I - uh,” Dean clears his throat and tries to step back, his mind fogging with their scent. Unfortunately, the one plastered to him just moves the same way, and the one on the desk looks at him with a pouty, hurt expression at the thought that Dean would ever try to distance himself from them. 

“What do you need, Dr. Winchester?” the one on the desk asks.

“It’s okay, sir,” the one against him adds. “You can tell us. We’re really good at keeping secrets. Aren’t we, Cas?”

The one on the desk - or, Cas, as Dean now knows - nods quickly. “Very good.”

“Maybe - maybe we should, uh - shit.” Dean’s eyes flutter closed as the one who must be Jimmy starts to rub himself against Dean. He can smell the waves of need coming from the boy, and he knows any second now that Cas' scent will be hitting him too. "Let's have this conversation in my office," Dean manages to choke out. 

Both boys perk up and grin. 

"Great idea," Cas says as he slides off the desk. 

The twins take each other's hands and begin to walk - though Dean would describe it more as a victorious kind of skip - to Dean's office. Dean is surprised they know exactly where it is, but then he realizes these two must have been checking him out as much as he's been checking them out. That helps his anxiety a little. The last thing he wanted was to come onto these two pretty little omegas only to find out he was wrong, getting himself in deep shit with the administration while also making the poor boys uncomfortable.

In case there was any confusion left, the second Dean closes his door, Cas and Jimmy are both pressed to his front, pinning Dean against the slab of wood. He barely manages to reach over and slide the lock into place. 

"What did you wanna talk about, Dr. Winchester?" Cas asks in a sing-song voice. 

Jimmy is bolder. "You could just show us, alpha."

Dean's self restraint snaps and he's reaching out with both arms. He fists Jimmy's hair in a tight grip and pulls him to his lips, having to slouch down to meet him for the kiss even though Jimmy is up in his toes. With his other hand, Dean is pulling Cas against his chest as tightly as he can. He devours Jimmy while sliding his huge hand down the back of Cas’ pretty shorts. Both boys are already moaning and panting, humping against him, and Dean feels like he might explode if he doesn't get inside of them soon. 

Cas is leaking so much slick, it must be dripping down his thighs by now. Dean's grateful. He drags his fingers through the mess and easily slides two of them inside the omega. Cas releases the most adorable little squeak, and then he's bouncing up and down on his tip-toes, trying desperately to fuck himself on Dean's fingers. 

Dean breaks his kiss with Jimmy so he can fully enjoy the show Cas is putting on. This doesn't bother Jimmy in the least. He just immediately falls to his knees and begins pulling at Dean's belt. 

Just as Dean feels cool air against his bare cock, both boys gasp. He looks at the two of them, then down at his cock since that's where the twins gazes are focused on. 

"So big, alpha," Jimmy whispers, bringing a tiny hand up to wrap around his cock. Dean groans when he sees that Jimmy's fingertips can't touch the tip of his thumb. 

"Gonna feel so good," Cas says in awe, so distracted by the cock he's no longer moving against Dean's fingers. 

Smiling, Dean asks, "You two ever taken an alpha's cock before?"

They both nod, still in a trance. 

Dean chuckles. "Mine is bigger, isn’t it?"

The twins nod, their tongues darting out to lick their lips at the exact same time. Dean watches them with hooded eyes as he wonders if they'll even be able to handle him. Dean's well above average. He's so hung, he's had a few omegas on the larger side struggle taking his cock. These boys are tiny. 

But, they aren't looking at his cock with fear or anxiety.

Oh no.

These two are staring at it like they've found the holy grail. 

"Who wants to ride it first?" Dean asks. 

Something shifts. Cas begins to pout, eyes dropping to the floor, and Jimmy grins wide. "I get to! I'm the oldest."

"Hmmm." Dean looks over at Cas, grabbing his chin and tugging upward so the boy is looking at him. "Jimmy can go first today, but you get to go first next time, okay?"

Cas' eyes widen. "But Jimmy always gets to go first."

"Not with me." Dean looks down at Jimmy and raises an eyebrow at him. "Understood?" 

Jimmy nods rapidly. "Yes, alpha. We can take turns."

"Good." Dean guides Jimmy's lips to his cock, groaning when his tongue darts out to taste it. When he realizes the boy's mouth is too small to take much, he gently pushes on Cas' head so he's kneeling too. Without being told, Cas leans in and starts to lap at the eight or so inches that Jimmy can't take down. Dean leans his head back and hums in appreciation. "That's it. Good boys. Good little omegas."

Two high pitched keens come from the floor but neither of the boys dare pull away from their alpha's cock. It makes Dean smile. He doesn’t care that he promised himself this is a one time thing. He doesn’t care that he already broke that promise by telling Cas he gets to go first next time. Because there’s going to be a next time. 

If Dean has his way, he’s going to spend the rest of his life having a next time with these two little sluts. 

"So patient. So good for your alpha," Dean coos. "I can smell you two. So horny. Desperate. Soaked with slick, making a mess on my floor. But no complaining. Just two good little omegas that want to make their alpha happy, aren't you?"

The twins whine and nod frantically, both working double time on his cock. He can see their bodies beginning to tremble with need. Can see the way their little bums twitch in excitement. Dean places a hand on each boy’s head, fisting their hair. He yanks them away from his cock and grins at the sight he’s shown. Flushed cheeks. Hooded blue eyes. Lips swollen and dripping with spit and precum. 

“Little sluts,” Dean growls.

Jimmy nods quickly, eyes going wider. “Yes, daddy.”

“Your little sluts, daddy” Cas clarifies. 

“Yes. You are,” Dean manages to whisper out as he stares at the two gorgeous boys. Them calling him daddy just revved every engine in Dean’s body. Even some he didn’t know existed. He’s caught between being breathlessly amazed and so horny he’s dizzy. He decides to take care of the horniness first. 

Dean uses his grip on their hair to pull them to their feet. They stumble a bit, but the wanton moans that pour from their pretty lips let Dean know they liked it. 

When they reach his couch, Dean lets go of them and tugs at their clothes. “Get naked.”

Dean’s not sure if he’s ever seen someone - or two someones - strip so damn fast. He’s pretty sure he hears fabric rip at some point, but it’s hard to tell between the rustle of clothing and the deep pants of the two boys. 

Once both sluts are naked, Dean picks Jimmy up with both hands. He tosses him onto the piece of furniture and easily settles him into the position he wants him to be in. Jimmy stays still when Dean moves away, keeping his legs tucked beneath him, lifted up on his knees just enough to create a few inches of space between his butt cheeks and his feet. His face is pressed against the cushion and his little hands lay loose at his sides. 

Can’t have that. 

After giving the boy’s pale ass a nice swat that makes him yelp and look up at Dean with wide eyes, Dean orders, “Reach back and spread your cheeks for me.”

Getting back in position, Jimmy does as told. The second his cheeks are pulled apart, a gush of slick comes pouring out of his twitching hole. It coats the back of Jimmy’s thighs as well as his feet that are just a few inches below. 

With a hand clamped down tight on the back of Cas’ neck, Dean pulls the boy in for a searing kiss. Once he has Cas’ breathless and humping against him, Dean gently pushes the boy away, pointing at Jimmy. “Your filthy slut of a brother made a mess. Go clean him, then prep him for daddy’s big cock with your fingers.”

Both boys moan at the same time. As Cas falls to his knees and begins to lap at his brother’s slick, Dean sits down in his office chair and relaxes. He kicks his pants off and slowly strokes his massive cock as he watches the boys with hooded eyes. Cas is already three fingers deep in his brother, tongue constantly lapping around his rim to try and catch all the slick pouring out of Jimmy. Dean knows he’s going to have to step in soon to prep Jimmy himself. Cas’ hands are too tiny. He could fist Jimmy and still not prepare him for Dean’s cock. 

Dean makes a mental note to buy them some toys they can use to prep themselves and each other when Dean doesn’t want to. He’s distracted by his mental note quickly, though. Jimmy is now taking Cas’ fist, head thrown back as he releases needy little sounds that might be too loud. After glancing at the door, Dean stands up and grabs Jimmy’s lace panties that are discarded on the floor. He leans down and stuffs Jimmy’s mouth full of the fabric, loving how pretty his puffy pink lips look wrapped around the black lace. 

“Why don’t you come here and suck daddy’s cock, baby?” Dean asks Cas, pulling his hand out of his brother and guiding him so he turns around. 

Without being urged further, Cas dives in and sucks Dean down as far as possible. Both of his small hands come up to rub and stroke the untouched space of his cock. Dean throws his head back and closes his eyes at the feel of Cas’ mouth mixed with slick soaked hands. He barely gets himself together enough to sink three fingers into Jimmy’s hole, groaning when just that is already making the boy whimper, his hole stretching further than his brother’s hand could do. 

Dean crooks his fingers, searching for Jimmy’s gland. He knows when he finds it. Jimmy’s entire body shudders violently and he screams into his panties. Plus, Dean’s hand goes from being coated in slick to absolutely drenched, the liquid gushing down his arm. 

Feeling himself losing all control, Dean begins to thrust into Cas’ mouth without concern for the boy and adds another finger to Jimmy. He can hear Cas gurgling and choking but ignores it as he tortures Jimmy using that perfect little spot inside of his chanel. By the time Dean’s fisting Jimmy himself, the little slut is so out of his mind that he doesn’t even register it. 

Knowing Jimmy is as ready as he’s going to be, Dean pulls his hand out and steps back from Cas. He groans when he catches a peak at Cas before the boy can wipe at his face. His eyes are red from crying, his flushed cheeks are coated in tears, his pink lips are swollen, and spit is dripping from his chin to his lap. 

Dean cups Cas’ face and strokes a thumb across his damp cheek, giving him a smile that’s soft for once. “Such a good boy for me. Did so well taking my cock. Daddy’s slutty little omega”

The boy shivers under the praise and turns his head to kiss the palm of Dean’s hand. 

Dean picks Jimmy up with an arm around his waist and sits down in the same spot the boy was just seconds ago. He presses Jimmy’s back to his chest and kisses his temple. “Come on, now. Ride daddy’s cock, baby. Take your time.”

With a needy whine, Jimmy begins to slowly move downward. The second Dean’s cock head breaches Jimmy’s hole, three things happen at once. Jimmy yowls into his gag, his chanel pulses so a new wave of gush comes out of him and coast Dean’s cock, and Dean loses control. He grabs Jimmy’s hips with bruising fingers and slams the boy onto him, needing to be in that tight heat. Needing to fuck and knot and claim. Jimmy’s lucky Dean only did this. If he lost complete control of himself, he’d have Jimmy pinned beneath him as he pounds his knot into the slut’s abused hole. 

Still, Jimmy is kicking his feet out, body writhing as he screams and shrieks and sobs into the lace panties. The whole time, though, the greedy little slut’s tiny cock is rock hard and leaking almost as much liquid as his hole is. 

Dean pushes Jimmy forward just enough to be able to look down and watch his massive cock in his tight little hole. 

“Come make your brother feel good, Cas,” Dean orders as he not-so-gently fucks up into Jimmy. When Castiel goes to take Jimmy’s cock in his mouth, Dean stops him with a hand on his throat. He uses the grip to guide Castiel forward until the boy is straddling both him and Jimmy, making it so the twins are face to face. “Jimmy, tell your brother how big daddy’s cock is.”

Jimmy reaches up and takes the panties out, thankful that Dean is slowing his movements so he doesn’t have to worry about screaming without the gag to keep him quiet. With a watery voice that matches his eyes, Jimmy tells Cas, “‘S soooo big, Cas. Fillin’ me so so good.”

Cas doesn’t have to be convinced of this. He can see their new alpha’s massive cock moving inside his brother’s small belly. In awe, he reaches out and places his hand on the bulge. Dean moans and bucks up against Jimmy so hard that Jimmy has to hurry to stuff his mouth again so he doesn’t get his alpha in trouble. 

“Yeah, baby,” Dean pants. “Keep doin’ that. Keep stroking your alpha through your brother’s belly. Good boy. Good omega.”

When Dean sees that Cas is so horny he’s grinding his little cock against his brother’s, he thinks of the perfect way to kill two birds with one stone. He can prep Cas - at least partially - while also keeping the boy occupied and included. 

“Ride Jimmy’s cock, little slut. Show daddy how desperate your greedy little hole is to be filled.”

Cheeks going pink, Cas inches forward until his brother’s cock is against his hole. It takes a few twitches and thrusts to get the cock that’s miniature compared to Dean’s, but big compared to Cas’ tight little hole, inside of Cas. When he throws his head back and keens, Dean rolls his eyes. 

He reaches over and grabs the lace panties from Jimmy’s mouth, pulling them halfway out. Then he grabs the hair at the back of Cas’ head and forces his face to press against Jimmy’s face. Cas understands what his alpha wants, gathering the fabric that’s outside of Jimmy’s mouth into his own, taking as much of it in as he can. By the time he’s finished, both boys have their mouths stuffed with soaked black lace, and their soft lips are pressed against each other. With each quick, brutal thrust of Dean’s, the boys are made to kiss each other around the lace. 

All of this is so overwhelming for Dean, his senses overloading. Between the sight of the two sweaty, tiny boys writhing in his lap, the feel of Jimmy’s tight little hole squeezing his cock, and the scent that the two boys’ are currently filling his office with, Dean’s right on the edge. 

Jimmy can feel it too. Oh boy can he feel it. He whimpers and squirms and actually tries to get off of Dean at one point, sobbing against Cas’ lips as the knot swells and swells and swells. 

One firm stroke from Cas through Jimmy’s belly and Dean’s popping his knot, slamming it past Jimmy’s rim so he’s tied to him. Jimmy blacks out, which is beautiful to watch. What’s even better is that Cas is so out of his mind himself that he continues riding Jimmy, who most likely just came inside of him. Each movement of the twin on top moves the twin on the bottom, making Dean feel as if he’s getting fucked even though the boy locked on his knot is passed out. 

“Feel good, little slut?” Dean asks as he reaches around Jimmy to stroke his own knot through the pale, thin skin. 

Cas moans and nods. 

“Come ride your daddy’s fingers. Much bigger.”

Blue eyes go wide, then the omega slut is pulling off of Jimmy’s spent cock and straddling Dean’s forearm, lowering himself onto the three fingers Dean is pointing toward the ceiling. The panties hang halfway out of Cas’ mouth now as he begins to ride Dean’s fingers, coating his hand and arm with slick. 

Dean continues stroking himself as he watches the show Cas is putting on for him. It’s helping milk his knot faster, which is exactly what he needs right now. Since he’s so big, Dean has unusually long knots, but he doesn’t want to make Cas wait long. At least not this time. In the future, his greedy little slut can wait his turn with a toy stuffed up his hole. Today, though, they’re all desperate to finish this. 

When Dean adds a fourth finger to Cas’ hole, Jimmy stirs away. He grinds down on Dean’s knot once and his tiny cock explodes with another orgasm. He shivers, teeth beginning to chatter. It takes a minute for his eyes to adjust. Then he notices Cas and groans, his poor omega cock filling with useless milk again. 

“Look so good like that,” Jimmy slurs as he turns his head and rests his cheek on Dean’s sweaty chest so he can relax and watch his brother. Dean lifts Jimmy’s hand and presses it to his knot. The boy doesn’t need to be told what to do. He just languidly strokes his alpha thrugh his belly as he watches his slutty twin make a spectacle of himself, now riding their daddy’s entire fist. 

“Alpha?” Jimmy asks as he squirms on his daddy’s cock. 

Dean hisses as his cock begins to pour more milk out from the stimulation, then answers, “What do you need, little omega?”

“Why didn’t you bite me?”

“Wh - what?”

“I woke up, ‘n I thought I’d have a claim, but I can’t feel it. You didn’t do it…”

Dean uses his free hand to turn Jimmy’s head so he can look into the boy’s big blue eyes. “I didn’t know if the two of you were ready to be claimed.”

“Mhhhhm!” Cas says into his gag, riding Dean’s fist even harder. “W’ wan’ ‘ou, ‘pha. Nee’ou.”

Since Cas is out of his mind with lust, Dean turns to Jimmy for confirmation. “Is that true? Do daddy’s good little ‘megas want to be claimed?”

Jimmy nods vigorously, and Dean can see Cas doing the same in his peripheral. “We’ve wanted you for so long, daddy.”

Cas whines his agreement into the lace panties. He shoots a dirty look at the hand Jimmy is using to stroke their daddy’s cock. Jealousy ignites in those baby blue eyes. 

“Jimmy, I think your brother wants daddy’s knot. Should we try to see if we can get you off?” 

With a little whimper and a nod, Jimmy perks up. He grips his alpha’s thighs to help stabilize himself. Dean guides him gently but lets Jimmy set the pace, not wanting to hurt the boy. His knot is lowered, but it’s not gone completely. 

Thankfully, Jimmy’s hole is gaping enough from the brutal fuck he just received that the knot pops out fairly easily, only drawing a grunt-like moan from him. 

“Now lick daddy clean so Cas can have a fresh cock to ride, Jimmy.”

Jimmy turns in his lap and lowers himself, taking Dean into his mouth. When he realizes that’s not going to work, he pulls away and starts to do little kitty licks with his tongue instead. It takes longer, but is much easier to do. By the time he’s finished, their alpha’s knot is gone completely, and his rock hard cock is waiting for a new omega. 

Cas wastes absolutely no time at all. He doesn’t even wait for Dean to help him or instruct him. He climbs onto his lap, facing the alpha unlike his brother, and immediately lowers himself onto his cock. He has the lace panties in his mouth, but he stills buries his face in Dean’s neck when he screams. When he gets about halfway down, his hole catches and fights him. Dean takes over from there, grabbing both of his butt cheeks and pulling them apart to make his hole open more. Cas slides down the rest of the way with a little squeak, then a very long moan. 

After that, all he can do is grip Dean’s shoulders for dear life and enjoy the ride. Dean’s needier now. Impatient. He wants to finish this so he can sink his teeth into these two pretty little omegas. Until they’re wearing his mark, he won’t be satisfied. It’s like there’s all of a sudden an itch beneath his skin. A fucking fire. And the only way to scratch it is to bite. To claim. 

“Jimmy,” Dean chokes out, grabbing Jimmy by the hair and tugging him close. He settles the boy next to Cas, one of his legs halfway in Cas’ lap so they’re slightly overlapping. With a strong hand, Dean guides Jimmy’s face to the other side of his neck, making him match Cas. “You two stay right there, okay?”

“Yes, daddy,” Jimmy whines. He’s pretty sure Cas does the same, but it’s hard to tell with the panties in his mouth. 

It doesn’t really matter. 

Dean has their permission already. Just the thought of that makes him fuck into Cas harder, feeling his knot begin to swell all over again. Cas starts writhing in desperation. Dean has to grip both boys’ heads at the back, using their hair to keep them firmly against his neck. He doesn’t want them pulling away. Not right now. Not when he needs them the most. 

Dean's already addicted. He needs to see this as often as possible. They're just so fucking little. The tiny sluts just take him, not caring that his cock distends their too-small bellies. 

“Daddy needs you both to be quiet, little ‘megas,” Dean growls as his knot pops past Cas’ rim. 

Just as the two boys are nodding to show they understand, Dean tightens his grip on Cas’ head and turns his own chin, grabbing the boy’s neck with his teeth and biting down until he tastes blood. He laps at it once, twice, then turns and does the exact same to Jimmy. 

Both boys go limp in his lap, Cas passed out and Jimmy drifting off somewhere fluffy and far away. 

“Mine,” Dean says firmly once he’s caught his breath. Neither boy answers - in fact, he’s pretty sure Jimmy is now sleeping too - but that doesn’t matter. He still repeats himself with a shit-eating grin. “All mine.”

**Author's Note:**

> Follow me on tumblr @ destiel-love-forever <3


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